2-(2,3-Dimethoxyphenyl)propan-2-ol

Base Information

• Chemical Name: 2-(2,3-Dimethoxyphenyl)propan-2-ol
• CAS No.: 153390-68-2
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.246
• NSC Number: 159481
• DSSTox Substance ID: DTXSID30303637
• Wikidata: Q82049018
• Mol file: 153390-68-2.mol

Synonyms:2-(2,3-dimethoxyphenyl)propan-2-ol;153390-68-2;NSC159481;DTXSID30303637;CS-M0279;AKOS016007251;NSC-159481;CS-14237;EN300-1841997

Chemical Property of 2-(2,3-Dimethoxyphenyl)propan-2-ol

Chemical Property:

• Boiling Point: 97 °C(Press: 0.5 Torr)
• PKA: 14.30±0.29(Predicted)
• Density: 1.060±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Dichloromethane, Ethyl acetate, Methanol
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 196.109944368
• Heavy Atom Count: 14
• Complexity: 179

Purity/Quality:

≥95% ^*data from raw suppliers

2-(2,3-Dimethoxyphenyl)propan-2-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C1=C(C(=CC=C1)OC)OC)O
• Uses: 2-(2,3-Dimethoxyphenyl)propan-2-ol is an intermediate of Miltirone (M344500), an active component in Salvia miltiorrhiza that has been shown to inhibit the increase in the abundance of the mRNA for the α4 subunit of the GABAA receptor induced by ethanol withdrawal in cultured hippocampal neurons. A potential phytotherapeutic agent in the treatment of alcohol dependence.

Technology Process of 2-(2,3-Dimethoxyphenyl)propan-2-ol

There total 5 articles about 2-(2,3-Dimethoxyphenyl)propan-2-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

methyl 2,3-dimethoxybenzoate (2150-42-7) + methylmagnesium bromide (75-16-1) → 2-<2,3-dimethoxyphenyl>-propan-2-ol (153390-68-2)

Guidance literature:

methyl 2,3-dimethoxybenzoate; methylmagnesium bromide; In tetrahydrofuran; at 20 ℃; for 22h; Reflux;

With water; ammonium chloride; In tetrahydrofuran;

DOI:10.1021/jo801914x

Reference yield: 45.0%

1,2-dimethoxybenzene (91-16-7) + acetone (67-64-1) → 2-<2,3-dimethoxyphenyl>-propan-2-ol (153390-68-2)

Guidance literature:

1,2-dimethoxybenzene; With n-butyllithium; In hexane; at 0 ℃; for 1h; Inert atmosphere;

acetone; In hexane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1055/a-1479-6005

Reference yield:

1,2-dimethoxybenzene (91-16-7) → 2-<2,3-dimethoxyphenyl>-propan-2-ol (153390-68-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

1.2: 98 percent / tetrahydrofuran / 15 h / 20 °C

2.1: 95 percent / tetrahydrofuran / 18 h / 60 °C

With n-butyllithium; In tetrahydrofuran;

DOI:10.1055/s-2004-837222

upstream raw materials:

methyl 2,3-dimethoxybenzoate

methylmagnesium bromide

1,2-dimethoxybenzene

acetone

Downstream raw materials:

2‐(5‐bromo‐2,3‐dimethoxyphenyl)propan‐2‐ol

5‐bromo‐1‐isopropyl‐2,3‐dimethoxybenzene

5-bromo-1-isopropenyl-2,3-dimethoxybenzene

4-[(E)-2-(3-Isopropyl-4,5-dimethoxy-phenyl)-vinyl]-3,3,4-trimethyl-cyclohexanone